Stereocontrolled palladium-catalysed umpolung allylation of aldehydes with allyl acetates
- verfasst von
- Monika Vogt, Sascha Ceylan, Andreas Kirschning
- Abstract
In the present work the stereocontrolled palladium-catalysed umpolung allylation of aldehydes is described. Allyl acetates are in situ transformed into the corresponding allyl boronates, which directly react with aldehydes. The question of stereocontrol is raised by employing (a) chiral boronating agents (reagent control) and by (b) utilising chiral aldehydes (substrate control). These studies reveal that the approach based on substrate control is superior to the former one with respect to yields and stereoselectivity. Remarkably, this umpolung protocol often yields the 4,5-syn products in high selectivity, which is unprecedented for direct crotylations.
- Organisationseinheit(en)
-
Institut für Organische Chemie
Zentrum für Biomolekulare Wirkstoffe (BMWZ)
- Typ
- Artikel
- Journal
- Tetrahedron
- Band
- 66
- Seiten
- 6450-6456
- Anzahl der Seiten
- 7
- ISSN
- 0040-4020
- Publikationsdatum
- 06.05.2010
- Publikationsstatus
- Veröffentlicht
- Peer-reviewed
- Ja
- ASJC Scopus Sachgebiete
- Biochemie, Wirkstoffforschung, Organische Chemie
- Elektronische Version(en)
-
https://doi.org/10.1016/j.tet.2010.04.133 (Zugang:
Unbekannt)
